Transparent plastic substrate and plastic lens

ABSTRACT

To provide a transparent plastic substrate having a high cut rate of blue light, a plastic lens and a transparent plastic member. A transparent plastic substrate containing a benzotriazole compound represented by the formula (1), a plastic lens containing the transparent plastic substrate, and a transparent plastic member containing a benzotriazole compound represented by the formula (1).

The present application is a divisional application of U.S. applicationSer. No. 16/113,603 filed Aug. 27, 2018, which in turn is a divisionalapplication of U.S. application Ser. No. 15/025,440 filed Mar. 28, 2016,which in turn is a National Stage Entry of PCT/JP2014/075963 filed onSep. 29, 2014, which claims the benefit of Japanese Patent ApplicationNo. 2013-205517 filed Sep. 30, 2013. The disclosures of the priorapplications are hereby incorporated by reference herein in theirentireties.

FIELD OF INVENTION

The present invention relates to a transparent plastic substrate, aplastic lens, and a transparent plastic member, and particularly relatesto a transparent plastic substrate and a plastic lens that have a highcut rate of blue light.

BACKGROUND ART

In a transparent plastic substrate and a plastic lens, the glare can bereduced, and the visibility and the contrast can be enhanced, by cuttinga light ray in the blue region (having a wavelength range of from 380 to500 nm). With respect to the health of eyes, a light ray in the blueregion (380 to 500 nm) has large energy and thus is said to be a factordamaging retina and the like. The damage due to blue light is referredto as “blue light hazard”, and light in the low wavelength side aroundfrom 380 to 420 nm is the most dangerous, and the light in the region issaid to be desirably cut.

For solving the problem, for example, PTL 1 proposes a lens having amultilayer film disposed on a convex surface of a plastic member, inwhich the multilayer film has an average reflectance of from 2 to 10% ina wavelength range of from 400 to 500 nm. However, the cut rate of bluelight measured for the lens is approximately 30%.

PTL 2 describes a polymerizable composition for a lens that contains abenzotriazole ultraviolet ray absorbent and is enhanced in light cutrate.

CITATION LIST Patent Literatures

PTL 1: JP-A-2012-093689

PTL 2: JP-A-2008-056854

SUMMARY OF INVENTION Technical Problem

An object of the present invention is to provide a transparent plasticsubstrate having a high cut rate of blue light, and a plastic lens and atransparent plastic member, each containing the same.

Solution to Problem

As a result of earnest investigations made by the present inventors forachieving the object, it has been found that the object can be achievedby adding an ultraviolet ray absorbent containing a benzotriazolecompound having a particular structure containing a group imparting amesomeric effect into a transparent plastic substrate, and thus thepresent invention has been completed.

The present invention thus provides the following items [1] to [3].

[1] A transparent plastic substrate containing a benzotriazole compoundrepresented by the following formula (1):

wherein R₁ represents an alkyl group having from 1 to 3 carbon atoms oran alkoxy group having from 1 to 3 carbon atoms; m represents an integerof 0 or 1; R₂ represents an alkyl group having from 1 to 12 carbon atomsor an alkoxy group having from 1 to 12 carbon atoms; R₃ represents ahydrogen atom or a divalent hydrocarbon group having from 1 to 8 carbonatoms; n represents a valence of the group represented by R₃, which is 1or 2, provided that in the case where m is 1, R₁ and R₂ may be the sameas or different from each other; and X represents a group imparting amesomeric effect.

[2] A plastic lens containing the transparent plastic substrateaccording to the item [1].

[3] A transparent plastic member containing the benzotriazole compoundrepresented by the formula (1).

Advantageous Effects of Invention

According to the present invention, a transparent plastic substratehaving a high cut rate of blue light, and a plastic lens and atransparent plastic member, each containing the same, can be provided.

DESCRIPTION OF EMBODIMENTS

The present description discloses the following embodiments shown initems (1) to (13).

-   (1) A transparent plastic substrate comprising a benzotriazole    compound represented by the following formula (1):

wherein R₁ represents an alkyl group having from 1 to 3 carbon atoms oran alkoxy group having from 1 to 3 carbon atoms; m represents an integerof 0 or 1; R₂ represents an alkyl group having from 1 to 12 carbon atomsor an alkoxy group having from 1 to 12 carbon atoms; R₃ represents ahydrogen atom or a divalent hydrocarbon group having from 1 to 8 carbonatoms; n represents a valence of the group represented by R₃, which is 1or 2, provided that in the case where m is 1, R₁ and R₂ may be the sameas or different from each other; and X represents a group imparting amesomeric effect.

-   (2) The transparent plastic substrate according to the above-item    (1), wherein X in the benzotriazole compound is at least one    selected from the group consisting of a chlorine atom, a bromine    atom, a fluorine atom, an iodine atom, a sulfo group, a carboxyl    group, a nitrile group, an alkoxy group, a hydroxyl group and an    amino group.-   (3) The transparent plastic substrate according to the above-item    (1), wherein the benzotriazole compound is represented by the    following general formula (1-1);

wherein R₁ represents an alkyl group having from 1 to 3 carbon atoms oran alkoxy group having from 1 to 3 carbon atoms; m represents an integerof 0 or 1; and R₂ represents an alkyl group having from 1 to 12 carbonatoms or an alkoxy group having from 1 to 12 carbon atoms, provided thatin the case where m is 1, R₁ and R₂ may be the same as or different fromeach other.

-   (4) The transparent plastic substrate according to any one of the    above-items (1) to (3), wherein the transparent plastic substrate    contains the benzotriazole compound in an amount in a range of from    0.05 to 3.00 parts by mass per 100 parts by mass of a resin    component comprising the transparent plastic substrate.-   (5) The transparent plastic substrate according to any one of the    above-items (1) to (4), wherein the benzotriazole compound is at    least one selected from    2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole,    2-(3-tert-butyl-2-hydroxy-5-ethylphenyl)-5-chloro-2H-benzotriazole,    2-(4-ethoxy-2-hydroxyphenyl)-5-chloro-2H-benzotriazole and    2-(4-butoxy-2-hydroxyphenyl)-5-chloro-2H-benzotriazole.-   (6) The transparent plastic substrate according to any one of the    above-items (1) to (5), wherein the transparent plastic substrate    has a cut rate of light in a wavelength range of from 380 to 500 nm    of 35% or more.-   (7) The transparent plastic substrate according to any one of the    above-items (1) to (6), wherein the transparent plastic substrate    has a cut rate of light having a wavelength of 410 nm of 50% or    more.-   (8) The transparent plastic substrate according to any one of the    above-items (1) to (7), wherein a resin component constituting the    transparent plastic substrate is at least one selected from the    group consisting of a (thio)urethane resin, an episulfide resin, a    polycarbonate resin, a polyamide resin, an acrylic resin, a vinyl    resin and a polyester resin.-   (9) A plastic lens comprising the transparent plastic substrate    according to any one of the above-items (1) to (8).-   (10) The plastic lens comprising the transparent plastic substrate    according to the above-item (9), wherein a resin component    constituting the transparent plastic substrate is a (thio)urethane    resin and/or an episulfide resin.-   (11) The plastic lens according to the above-item (10), wherein a    monomer forming the transparent plastic substrate is a combination    of an aliphatic polyisocyanate compound and/or an alicyclic    polyisocyanate compound, and a polythiol compound.-   (12) A transparent plastic member comprising a benzotriazole    compound represented by the following formula (1):

wherein R₁ represents an alkyl group having from 1 to 3 carbon atoms oran alkoxy group having from 1 to 3 carbon atoms; m represents an integerof 0 or 1; R₂ represents an alkyl group having from 1 to 12 carbon atomsor an alkoxy group having from 1 to 12 carbon atoms; R₃ represents ahydrogen atom or a divalent hydrocarbon group having from 1 to 8 carbonatoms; n represents a valence of the group represented by R₃, which is 1or 2, provided that in the case where m is 1, R₁ and R₂ may be the sameas or different from each other; and X represents a group imparting amesomeric effect.

-   (13) The transparent plastic member according to the above-item    (12), wherein a transparent plastic member comprises a transparent    plastic substrate and a functional layer, and the benzotriazole    compound represented by the formula (1) is contained in any of the    transparent plastic substrate and the functional layer.

The transparent plastic substrate of the present invention contains thebenzotriazole compound represented by the formula (1) as an ultravioletray absorbent.

In the formula (1), X represents a group imparting a mesomeric effect.It is expected that the group imparting a mesomeric effect present onthe benzotriazole ring enhances the cut rate of blue light.

The substitution position of X is preferably the 5-position of thetriazole ring.

Examples of X include a chlorine atom, a bromine atom, a fluorine atom,an iodine atom, a sulfo group, a carboxyl group, a nitrile group, analkoxy group, a hydroxyl group and an amino group, and among these, achlorine atom, a bromine atom and a fluorine atom are preferred, and achlorine atom is more preferred.

In the formula (1), R₂ represents an alkyl group having from 1 to 12carbon atoms or an alkoxy group having from 1 to 12 carbon atoms, andfor each of the alkyl group and the alkoxy group, the number of carbonatoms is preferably from 1 to 8, more preferably from 2 to 8, andfurther preferably from 4 to 8.

The alkyl group and the alkoxy group each may be branched or linear.Among the alkyl group and the alkoxy group, the alkyl group ispreferred.

Examples of the alkyl group include a methyl group, an ethyl group, an-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group,a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an-octyl group, a 1,1,3,3-tetramethylbutyl group, a nonyl group, a decylgroup, an undecyl group and a dodecyl group, and among these, at leastone selected from a n-propyl group, an isopropyl group, a n-butyl group,a sec-butyl group, a tert-butyl group and a 1,1,3,3-tetramethylbutylgroup is preferred, a n-butyl group, a sec-butyl group, a tert-butylgroup and a 1,1,3,3-tetramethylbutyl group are more preferred, and atert-butyl group is further preferred.

Examples of the alkoxy group include a methoxy group, an ethoxy group, apropoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, aheptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group,an undecyloxy group and a dodecyloxy group, and among these, a butoxygroup and an ethoxy group are preferred.

In the formula (1), the substitution position of R₂ is preferably the3-position, the 4-position or the 5-position with respect to thesubstitution position of the benzotriazolyl group.

In the formula (1), R₁ represents an alkyl group having from 1 to 3carbon atoms or an alkoxy group having from 1 to 3 carbon atoms, andspecific examples thereof include the groups described for R₂ thatconform in the number of carbon atoms. Among the groups, a methyl groupand an ethyl group are preferred. In the case where R₁ is one of thesegroups, an excellent cut rate of blue light is obtained. In the casewhere the number of carbon atoms of R₁ is 4 or more (for example,2-(3,5-di-t-butyl-2-hydroxyphenyl)-5-chlorobenzotriazole), the compoundis a persistent compound, which has a large environment load and maybring possible influence to human body, and thus may be designated as amanufacturing prohibited substance in some cases. However, the compoundof the formula (1) can be decomposed relatively easily, and also has anadvantage of less influence on human body.

In the formula (1), m represents an integer of 0 or 1.

In the formula (1), the substitution position of R₂ is preferably the5-position with respect to the substitution position of thebenzotriazolyl group.

In the formula (1), R₃ represents a hydrogen atom or a divalenthydrocarbon group having from 1 to 8 carbon atoms, and among these, ahydrogen atom is preferred.

Examples of the hydrocarbon group represented by R₃ include an aliphatichydrocarbon group and an aromatic hydrocarbon group.

The hydrocarbon group represented by R₃ preferably has from 1 to 8carbon atoms, and more preferably from 1 to 3 carbon atoms.

Examples of the divalent hydrocarbon group represented by R₃ include amethanediyl group, an ethanediyl group, a propanediyl group, abenzenediyl group and toluenediyl group, and among these, a methanediylgroup is preferred.

n represents a valence of the group represented by R₃, which is 1 or 2.

In the formula (1), the substitution position of R₃ is preferably the3-position with respect to the substitution position of thebenzotriazolyl group.

R₃ preferably represents a hydrogen atom, and in this case, n is 1.

The triazole compound is preferably a compound represented by thefollowing formula (1-1):

In the formula, R₁, R₂ and m are the same as the examples and thepreferred embodiments described above.

Specific examples of the benzotriazole compound represented by theformula (1) includemethylenebis(3-(5-chloro-2-benzotriazolyl)-5-(1,1,3,3-tetramethylbutyl)-2-hydroxyphenyl),methylenebis(3-(5-chloro-2-benzotriazolyl)-5-(tert-butyl)-2-hydroxyphenyl),methylenebis(3-(5-chloro-2-benzotriazolyl)-5-tert-butyl-2-hydroxyphenyl),methylenebis(3-(5-chloro-2-benzotriazolyl)-5-ethoxy-2-hydroxyphenyl),phenylenebis(3-(5-chloro-2-benzotriazolyl)-5-(1,1,3,3-tetramethylbutyl)-2-hydroxyphenyl), and specific examples of the benzotriazole compound representedby the formula (1-1) described below.

Specific examples of the benzotriazole compound represented by theformula (1-1) include2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole,2-(3-tert-butyl-2-hydroxy-5-ethylphenyl)-5-chloro-2H-benzotriazole,5-chloro-2-(3,5-dimethyl-2-hydroxyphenyl)-2H-benzotriazole,5-chloro-2-(3,5-diethyl-2-hydroxyphenyl)-2H-benzotriazole,5-chloro-2-(2-hydroxy-4-methoxyphenyl)-2H-benzotriazole,5-chloro-2-(4-ethoxy-2-hydroxyphenyl)-2H-benzotriazole,2-(4-butoxy-2-hydroxyphenyl)-5-chloro-2H-benzotriazole and5-chloro-2-(2-hydroxy-4-octyloxyphenyl)-2H-benzotriazole.

Among these,2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole,2-(3-tert-butyl-2-hydroxy-5-ethylphenyl)-5-chloro-2H-benzotriazole,5-chloro-2-(4-ethoxy-2-hydroxyphenyl)-2H-benzotriazole and2-(4-butoxy-2-hydroxyphenyl)-5-chloro-2H-benzotriazole are preferred.

The transparent plastic substrate of the present invention preferablycontains the benzotriazole compound that is used in an amount in a rangeof from 0.05 to 3.00 parts by mass, more preferably from 0.05 to 2.50parts by mass, further preferably from 0.10 to 2.00 parts by mass, andstill further preferably from 0.30 to 2.00 parts by mass, per 100 partsby mass of the resin component (i.e., a monomer and/or a polymer)constituting the transparent plastic substrate. The amount of thebenzotriazole compound added may vary depending on the kind of the resincomponent, the target ultraviolet ray absorbing characteristics, and thelike.

The resin component constituting the transparent plastic substrate ispreferably at least one selected from the group consisting of a(thio)urethane resin, an episulfide resin, a polycarbonate resin, apolyamide resin, an acrylic resin, a vinyl resin and a polyester resin,and in the case where the transparent plastic substrate is a plasticlens, a (thio)urethane resin and/or an episulfide resin are preferred.

A (thio)urethane resin herein means at least one selected from aurethane resin and a thiourethane resin.

A monomer for forming the (thio)urethane resin in the invention is a rawmaterial monomer for producing a polythiourethane lens or a polyurethanelens, and specific examples thereof include a combination of apolyisocyanate compound and a polythiol compound, and a combination of apolyisocyanate compound and a polyol compound.

The polyisocyanate compound is not particularly limited, and specificexamples thereof include an alicyclic isocyanate compound, such as,bis(isocyanatomethyl)cyclohexane,bis(isocyanatomethyl)bicyclo[2.2.1]heptane, hydrogenated 2,6-tolylenediisocyanate, hydrogenated m- and p-phenylene diisocyanate, hydrogenated2,4-tolylene diisocyanate, hydrogenated diphenylmethane diisocyanate,hydrogenated m-xylylene diisocyanate, hydrogenated p-xylylenediisocyanate and isophorone diisocyanate; an isocyanate compound thathas an alicyclic ring or an aromatic ring, such as, m- and p-phenylenediisocyanate, 2,6-tolylene diisocyanate, 2,4-tolylene diisocyanate,4,4′-diphenylmethane diisocyanate, m- and p-xylylene diisocyanate(bis(isocyanatomethyl)benzene), m- and p-tetramethylxylylenediisocyanate, 2,6-naphthalene diisocyanate, 1,5-naphthalenediisocyanate, hexamethylene diisocyanate, octamethylene diisocyanate,2,2,4-trimethylhexamethylene diisocyanate, tetramethylene diisocyanate,a biuret reaction product of hexamethylene diisocyanate, a trimer ofhexamethylene diisocyanate, lysine diisocyanate, lysine triisocyanate,1,6,11-undecane triisocyanate and triphenylmethane triisocyanate; and asulfur-containing isocyanate compound, such as, diphenyldisulfide-4,4′-diisocyanate, 2,2′-dimethyldiphenyldisulfide-5,5′-diisocyanate, 3,3′-dimethyldiphenyldisulfide-5,5′-diisocyanate, 3,3′-dimethyldiphenyldisulfide-6,6′-diisocyanate, 4,4′-dimethyldiphenyldisulfide-5,5′-diisocyanate, 3,3′-dimethoxydiphenyldisulfide-4,4′-diisocyanate, 4,4′-dimethoxydiphenyldisulfide-3,3′-diisocyanate, diphenylsulfone-4,4′-diisocyanate,diphenylsulfone-3,3′-diisocyanate, benzylidenesulfone-4,4′-diisocyanate,diphenylmethanesulfone-4,4′-diisocyanate,4-methyldiphenylmethanesulfone-2,4′-diisocyanate,4,4′-dimethoxydiphenylsulfone-3,3′-diisocyanate,3,3′-dimethoxy-4,4′-diisocyanatodibenzylsulfone,4,4′-dimethyldiphenylsulfone-3,3′-diisocyanate,4,4′-di-tert-butyldiphenylsulfone-3,3′-diisocyanate,4,4′-dimethoxybenzeneethylenesulfone-3,3′-diisocyanate,4,4′-dichlorodiphenylsulfone-3,3′-diisocyanate,4-methyl-3-isocyanatobenzenesulfonyl-4′-isocyanatophenol ester,4-methoxy-3-isocyanatobenzenesulfonyl-4′-isocyanatophenol ester,4-methyl-3-isocyanatobenzenesulfonylanilide-3′-methyl-4′-isocyanate,dibenzenesulfonyl-ethylenediamine-4,4′-diisocyanate,4,4′-dimethoxybenzenesulfonyl-ethylenediamine-3,3 diisocyanate,4-methyl-3-isocyanatobenzenesulfonylanilide-4-methyl-3′-isocyanate,thiophene-2,5-diisocyanate, thiophene-2,5-diisocyanatomethyl,1,4-dithiane-2,5-diisocyanate, 1,4-dithiane-2,5-diisocyanatomethyl,1,4-dithiane-2,3-diisocyanatomethyl,1,4-dithiane-2-isocyanatomethyl-5-isocyanatopropyl,1,3-dithiolane-4,5-diisocyanate, 1,3-dithiolane-4,5-diisocyanatomethyl,1,3-dithiolane-2-methyl-4,5-diisocyanatomethyl,1,3-dithiolane-2,2-diisocyanatoethyl,tetrahydrothiophene-2,5-diisocyanate,tetrahydrothiophene-2,5-diisocyanatomethyl,tetrahydrothiophene-2,5-diisocyanatoethyl andtetrahydrothiophene-3,4-diisocyanatomethyl. Among these, an alicyclicisocyanate compound is preferred.

Examples of the polythiol compound include an aliphatic thiol, such as,methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol,1,2-propanedithiol, 1,3-propanedithiol, 2,2-propanedithiol,1,6-hexanedithiol, 1,2,3-propanetrithiol,tetrakis(mercaptomethyl)methane, 1,1-cyclohexanedithiol,1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol,3,4-dimethoxybutane-1,2-dithiol, 2-methylcyclohexane-2,3-dithiol,1,1-bis(mercaptomethyl)cyclohexane, thiomalic acid bis(2-mercaptoethylester), 2,3-dimercaptosuccinic acid (2-mercaptoethyl ester),2,3-dimercapto-1-propanol (2-mercaptoacetate), 2,3-dimercapto-1-propanol(3-mercaptoacetate), diethylene glycol bis(2-mercaptoacetate),diethylene glycol bis(3-merecaptopropionate), 1,2-dimercaptopropylmethyl ether, 2,3-dimercaptopropyl methyl ether,2,2-bis(mercaptomethyl)-1,3-propanedithiol, bis(2-mercaptoethyl) ether,ethylene glycol bis(2-mercaptoaectate), ethylene glycolbis(3-mercaptopropionate), trimethylolpropane tris(2-mercaptoacetate),trimethylolpropanetris(3-mercaptopropionate), pentaerythritoltetrakis(2-mercaptoacetate), pentaerythritoltetrakis(3-mercaptopropionate) and1,2-bis(2-mercaptoethylthio)-3-mercaptopropane; an aromatic thiol, suchas, 1,2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene,1,2-bis(mercaptomethyl)benzene, 1,3-bis(mercaptomethyl)benzene,1,4-bis(mercaptomethyl)benzene, 1,3-bis(mercaptoethyl)benzene,1,4-bis(mercaptoethyl)benzene, 1,2-bis(mercaptomethoxy)benzene,1,3-bis(mercaptomethoxy)benzene, 1,4-bis(mercaptomethoxy)benzene,1,2-bis(mercaptoethoxy)benzene, 1,3-bis(mercaptoethoxy)benzene,1,4-bis(mercaptoethoxy)benzene, 1,2,3-trimercaptobenzene,1,2,4-trimercaptobenzene, 1,3,5-trimercaptobenzene,1,2,3-tris(mercaptomethyl)benzene, 1,2,4-tris(mercaptomethyl)benzene,1,3,5-tris(mercaptomethyl)benzene, 1,2,3-tris(mercaptoethyl)benzene,1,2,4-tris(mercaptoethyl)benzene, 1,3,5-tris(mercaptoethyl)benzene,1,2,3-tris(mercaptomethoxy)benzene, 1,2,4-tris(mercaptomethoxy)benzene,1,3,5-tris(mercaptomethoxy)benzene, 1,2,3-tris(mercaptoethoxy)benzene,1,2,4-tris(mercaptoethoxy)benzene, 1,3,5-tris(mercaptoethoxy)benzene,1,2,3,4-tetramercaptobenzene, 1,2,3,5-tetramercaptobenzene,1,2,4,5-tetramercaptobenzene, 1,2,3,4-tetrakis(mercaptomethyl)benzene,1,2,3,5-tetrakis(mercaptomethyl)benzene,1,2,4,5-tetrakis(mercaptomethyl)benzene,1,2,3,4-tetrakis(mercaptoethyl)benzene,1,2,3,5-tetrakis(mercaptoethyl)benzene,1,2,4,5-tetrakis(mercaptoethyl)benzene,1,2,3,4-tetrakis(mercaptoethyl)benzene,1,2,3,5-tetrakis(mercaptomethoxy)benzene,1,2,4,5-tetrakis(mercaptomethoxy)benzene,1,2,3,4-tetrakis(mercaptoethoxy)benzene,1,2,3,5-tetrakis(mercaptoethoxy)benzene,1,2,4,5-tetrakis(mercaptoethoxy)benzene, 2,2′-dimercaptobiphenyl,4,4′-dimercaptobiphenyl, 4,4′-dimercaptobibenzyl, 2,5-toluenedithiol,3,4-toluenedithiol, 1,4-naphthalenedithiol, 1,5-naphthalenedithiol,2,6-naphthalene dithiol, 2,7-naphthalenedithiol,2,4-dimethylbenzene-1,3-dithiol, 4,5-dimethylbenzene-1,3-dithiol,9,10-anthracenedimethanethiol,1,3-di(p-methoxyphenyl)propane-2,2-dithiol,1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol and2,4-di(p-mercaptophenyl)pentane; a halogen-substituted aromatic thiol,including a chlorine-substituted compound and a bromine-substitutedcompound, such as, 2,5-dichlorobenzene-1,3-dithiol,1,3-di(p-chlorophenyl)propane-2,2-dithiol,3,4,5-tribromo-1,2-dimercaptobenzene and2,3,4,6-tetrachloro-1,5-bis(mercaptomethyl)benzene; an aromatic thiolcontaining a sulfur atom other than a mercapto group, such as,1,2-bis(mercaptomethylthio)benzene, 1,3-bis(mercaptomethylthio)benzene,1,4-bis(mercaptomethylthio)benzene, 1,2-bis(mercaptoethylthio)benzene,1,3-bis(mercaptoethylthio)benzene, 1,4-bis(mercaptoethylthio)benzene,1,2,3-tris(mercaptomethylthio)benzene,1,2,4-tris(mercaptomethylthio)benzene,1,3,5-tris(mercaptomethylthio)benzene,1,2,3-tris(mercaptoethylthio)benzene,1,2,4-tris(mercaptoethylthio)benzene,1,3,5-tris(mercaptoethylthio)benzene,1,2,3,4-tetrakis(mercaptomethylthio)benzene,1,2,3,5-tetrakis(mercaptomethylthio)benzene,1,2,4,5-tetrakis(mercaptomethylthio)benzene,1,2,3,4-tetrakis(mercaptoethylthio)benzene,1,2,3,5-tetrakis(mercaptoethylthio)benzene,1,2,4,5-tetrakis(mercaptoethylthio)benzene, and nuclear alkylatedcompounds thereof, an aliphatic thiol containing a sulfur atom otherthan a mercapto group, such as, bis(mercaptomethyl) sulfide,bis(mercaptoethyl) sulfide, bis(mercaptopropyl) sulfide,bis(mercaptomethylthio)methane, bis(2-mercaptoethylthio)methane,bis(3-mercaptopropylthio)methane, 1,2-bis(mercaptomethylthio)ethane,1,2-bis(2-mercaptoethylthio)ethane, 1,2-bis(3-mercaptopropylthio)ethane,1,3-bis(mercaptomethylthio)propane, 1,3-bis(2-mercaptoethylthio)propane,1,3-bis(3-mercaptopropylthio)propane,1,2-bis(2-mercaptoethylthio)-3-mercaptopropane,2-mercaptoethylthio-1,3-propanedithiol,1,2,3-tris(mercaptomethylthio)propane,1,2,3-tris(2-mercaptoethylthio)propane,1,2,3-tris(3-mercaptopropylthio)propane,tetrakis(mercaptomethythiomethyl)methane,tetrakis(2-mercaptoethylthiomethyl)methane,tetrakis(3-mercaptopropylthiomethyl)methane,bis(2,3-dimercaptopropyl)sulfide, 2,5-dimercapto-1,4-dithiane,bis(mercaptomethyl) disulfide, bis(mercaptoethyl) disulfide,bis(mercaptopropyl) disulfide, and esters of these compounds withthioglycolic acid and mercaptopropionic acid, hydroxymethyl sulfidebis(2-mercaptoacetate), hydroxymethyl sulfide bis(3-mercaptopropionate),hydroxyethyl sulfide bis(2-mercaptoacetate), hydroxyethyl sulfidebis(3-mercaptopropyonate), hydroxypropyl sulfide bis(2-mercaptoacetate),hydroxypropyl sulfide bis(3-mercaptopropionate), hydroxymethyl disulfidebis(2-mercaptoacetate), hydroxymethyl disulfidebis(3-mercaptopropionate), hydroxyethyl disulfidebis(2-mercaptoacetate), hydroxyethyl disulfidebis(3-mercaptopropionate), hydroxypropyl disulfidebis(2-mercaptoacetate), hydroxypropyl disulfidebis(3-mercaptopropionate), 2-mercaptoethyl ether bis(2-mercaptoacetate),2-mercaptoethyl ether bis(3-mercaptopropionate), 1,4-dithiane-2,5-diolbis(2-mercaptoacetate), 1,4-dithiane-2,5-diol bis(3-mercaptopropionate),thioglycolic acid (2-mercaptoethyl ester), thiothpropionic acidbis(2-mercaptoethyl ester), 4,4′-thiodibutyric acid bis(2-mercaptoethylester), dithiodiglycolic acid bis(2-mercaptoethyl ester),dithiodipropionic acid bis(2-mercaptoethyl ester), 4,4′-dithiodibtyricacid bis(2-mercaptoethyl ester), thiodiglycolic acidbis(2,3-dimercaptopropyl ester), thiodipropionic acidbis(2,3-dimercaptopropyl ester), dithiodiglycolic acidbis(2,3-dimercaptopropyl ester), dithiodipropionic acidbis(2,3-dimercaptopropyl ester),4-mercaptomethyl-3,6-dithiaoctane-1,8-dithiol,bis(mercaptomethyl)-3,6,9-trithia-1,11-undecanedithiol andbis(1,3-dimercapto-2-propyl) sulfide; and a heterocyclic compoundcontaining a sulfur atom other than a mercapto group, such as,3,4-thiophenedithiol, tetrahydrothiophene-2,5-dimercaptomethyl,2,5-dimercapto-1,3,4-thiadiazole, 2,5-dimercapto-1,4-dithiane and2,5-dimercaptomethyl-1,4-dithiane.

Examples of the polyol compound include an aliphatic polyol, such as,ethylene glycol, diethylene glycol, propylene glycol, dipropyleneglycol, butylene glycol, neopentyl glycol, glycerin, trimethylolethane,trimethylolpropane, butanetriol, 1,2-methylglycoside, pentaerythritol,dipentaerythritol, tripentaerythritol, triethylene glycol, polyethyleneglycol, tris(2-hydroxyethyl) isocyanurate, cyclobutanediol,cyclopentanediol, cyclohexanediol, cycloheptanediol, cyclooctanediol,bicyclo[4.3.0]nonanediol, dicyclohexanediol,tricyclo[5.3.1.1]dodecanediol, spiro[3.4]octanediol andbutylcyclohexanediol; an aromatic polyol, such as, dihydroxynaphthalene,trihydroxynaphthalene, tetrahydroxynaphthalene, dihydroxybenzene,benzenetriol, trihydroxyphenanthrene, bisphenol A, bisphenol F, xylyleneglycol and tetrabromobisphenol A, and addition reaction products ofthese compounds with an alkylene oxide, such as, ethylene oxide andpropylene oxide; bis(4-(hydroxyethoxy)phenyl) sulfide,bis(4-(2-hydroxypropoxy)phenyl) sulfide,bis(4-(2,3-dihydroxypropoxy)phenyl) sulfide,bis(4-(4-hydroxycyclohexyloxy)phenyl) sulfide,bis(2-methyl-4-(hydroxyethoxy)-6-butylphenyl) sulfide, and thesecompounds having ethylene oxide and/or propylene oxide added thereto inan amount of 3 molecules in average or less per one hydroxyl group; anda polyol containing a sulfur atom, such as, di(2-hydroxyethyl) sulfide,1,2-bis(2-hydroxyethylmercapto)ethane, bis(2-hydroxyethyl) disulfide,1,4-dithiane-2,5-diol, bis(2,3-dihydroxypropyl) sulfide,tetrakis(4-hydroxy-2-thiabutyl)methane, bis(4-hydroxyphenyl)sulfone(trade name: bisphenol S), tetrabromobisphenol S, tetramethylbisphenolS, 4,4′-thiobis(6-tert-butyl-3-methylphenol) and1,3-bis(2-hydroxyethylthioethyl)cyclohexane.

The monomer for forming the (thio)urethane resin has been known, andspecific examples of the known publications that describe the monomerinclude JP-A-58-127914, JP-A-57-136601, JP-A-01-163012, JP-A-03-236386,JP-A-03-281312, JP-A-04-159275, JP-A-05-148340, JP-A-06-065193,JP-A-06-256459, JP-A-06-313801, JP-A-06-192250, JP-A-07-063902,JP-A-07-104101, JP-A-07-118263, JP-A-07-118390, JP-A-07-316250,JP-A-60-199016, JP-A-60-217229, JP-A-62-236818, JP-A-62-255901,JP-A-62-267316, JP-A-63-130615, JP-A-63-130614, JP-A-63-046213,JP-A-63-245421, JP-A-63-265201, JP-A-01-090167, JP-A-01-090168,JP-A-01-090169, JP-A-01-090170, JP-A-01-096208, JP-A-01-152019,JP-A-01-045611, JP-A-01-213601, JP-A-01-026622, JP-A-01-054021,JP-A-01-311118, JP-A-01-295201, JP-A-01-302202, JP-A-02-153302,JP-A-01-295202, JP-A-02-802, JP-A-02-036216, JP-A-02-058517,JP-A-02-167330, JP-A-02-270859, JP-A-03-84031, JP-A-03-084021,JP-A-03-124722, JP-A-04-78801, JP-A-04-117353, JP-A-04-117354,JP-A-04-256558, JP-A-05-78441, JP-A-05-273401, JP-A-05-093801,JP-A-05-080201, JP-A-05-297201, JP-A-05-320301, JP-A-05-208950,JP-A-06-072989, JP-A-06-256342, JP-A-06-122748, JP-A-07-165859,JP-A-07-118357, JP-A-07-242722, JP-A-07-247335, JP-A-07-252341,JP-A-08-73732, JP-A-08-092345, JP-A-07-228659, JP-A-08-3267,JP-A-07-252207, JP-A-07-324118 and JP-A-09-208651. The polyisocyanatecompounds, the polyol compounds and the polythiol compounds described inthese publications correspond to the (thio)urethane monomers in thepresent invention. A monomer forming the episulfide resin describedlater, and other monomers, such as, diethylene glycol allyl carbonate,may be added to these monomers for modifying the properties, includingthe heat resistance and the refractive index.

The monomer for forming the episulfide resin in the present inventionmay also be referred to as a monomer forming an epithio structure, andmeans a monomer having an episulfide group (epithio group) and a monomermixture containing the monomer. Specific examples of the monomer havingan episulfide group include an episulfide compound having an alicyclicstructure, such as, 1,3- and 1,4-bis(β-epithiopropylthio)cyclohexane,1,3- and 1,4-bis(β-epithiopropylthiomethyl)cyclohexane,bis(4-(β-epithiopropylthio)cyclohexyl)methane,2,2-bis(4-(β-epithiopropylthio)cyclohexyl)propane andbis(4-(β-epithiopropylthio)cyclohexyl) sulfide; an episulfide compoundhaving an aromatic structure, such as, 1,3- and1,4-bis(β-epithiopropylthio)benzene, 1,3- and1,4-bis(β-epithiopropylthiomethyl)benzene,bis(4-(β-epithiopropylthio)phenylmethane,2,2-bis(4-(β-epithiopropylthio)phenyl)propane,bis(4-(β-epithiopropylthio)phenyl) sulfide,bis(4-(β-epithiopropylthio)phenyl)sulfine and4,4-bis(β-epithiopropylthio)biphenyl; an episulfide compound having adithiane ring structure, such as,2,5-bis(β-epithiopropylthiomethyl)-1,4-dithiane,2,5-bis(β-epithiopropylthioethylthiomethyl)-1,4-dithiane,2,5-bis(β-epithiopropylthioethyl)-1,4-dithiane and2,3,5-tri(β-epithiopropylthioethyl)-1,4-dithiane; and an episulfidecompound having an aliphatic structure, such as,2-(2-β-epithiopropylthioethylthio)-1,3-bis(β-epithiopropylthio)propane,1,2-bis(β-epithiopropylthioethyl)thio)-3-(β-epithiopropylthio)propane,tetrakis(β-epithiopropylthiomethyl)methane,1,1,1-tris(β-epithiopropylthiomethyl)propane and bis(β-epithiopropyl)sulfide.

The monomer forming the episulfide resin has been known, and specificexamples of the known publications therefor include JP-A-09-071580,JP-A-09-110979, JP-A-09-255781, JP-A-03-081320, JP-A-11-140070,JP-A-11-183702, JP-A-11-189592, JP-A-11-180977 and JP-A-01-810575. Theepisulfide monomers described in these publications correspond to theepisulfide monomers in the present invention. Other monomers for thetransparent plastic substrate such as, a monomer for forming the(thio)urethane resin may be added for modifying the lens properties suchas, the impact resistance and the processability.

In the present invention, a diethylene glycol bisallyl carbonate monomeras an optional component may be added to the monomer forming the(thio)urethane resin and/or the episulfide resin.

As the diethylene glycol bisallyl carbonate monomer, applicable are solediethylene glycol bisallyl carbonate, and a monomer mixture containingdiethylene glycol bisallyl carbonate and a monomer that iscopolymerizable therewith. Specific examples of the copolymerizablemonomer include an aromatic vinyl compound, such as, styrene,α-methylstyrene, vinyltoluene, chlorostyrene, chloromethylstyrene anddivinylbenzene; a mono(meth)acrylate compound, such as, methyl(meth)acrylate, n-butyl (meth)acrylate, n-hexyl (meth)acrylate,cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate,methoxydiethylene glycol (meth)acrylate, methoxypolyethylene glycol(meth)acrylate, 3-chloro-2-hydroxypropyl (meth)acrylate, stearyl(meth)acrylate, lauryl (meth)acrylate, phenyl (meth)acrylate, glycidyl(meth)acrylate and benzyl methacrylate; a mono(meth)acrylate compoundhaving a hydroxyl group, such as, 2-hydroxyethyl (meth)acrylate,2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate,3-phenoxy-2-hydroxypropyl (meth)acrylate and 4-hydroxybutyl(meth)acrylate; a di(meth)acrylate compound, such as, ethylene glycoldi(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycoldi(meth)acrylate, polyethylene glycol di(meth)acrylate, 1,3-butyleneglycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, neopentylglycol di(meth)acrylate, polypropylene glycol di(meth)acrylate,2-hydroxy-1,3-di(meth)acryloxypropane,2,2-bis(4-((meth)acryloxyethoxy)phenyl)propane,2,2-bis(4-((meth)acryloxy-diethoxy)phenyl)propane and2,2-bis(4-((meth)acryloxy-polyethoxy)phenyl)propane; a tri(meth)acrylatecompound, such as, trimethylolpropane trimethacrylate andtetramethylolmethane trimethacrylate; a tetra(meth)acrylate compound,such as, tetramethylolmethane tetra(meth)acrylate (provided that theterm (meth)acrylate in the description means methacrylate or acrylate);diallyl phthalate, diallyl isophthalate, diallyl terephthalate.

In the transparent plastic substrate of the present invention, in thecase where the monomer having a thiourethane structure is used as a maincomponent, the transparent plastic substrate is preferably polymerizedfrom a raw material having a total mass of the polyisocyanate compoundand the polythiol compound as the raw material monomers of 0.6 or morewith respect to the total mass of the raw material monomers being 1.

In the case where the monomer forming the episulfide resin is used as amain component, the transparent plastic substrate is preferablypolymerized from a raw material having an amount of the compound havingan episulfide group as the raw material monomer of 0.6 or more withrespect to the total mass of the raw material monomers being 1.

Examples of the production method of the transparent plastic substrateof the present invention include a method of mixing at least one kind ofthe benzotriazole compound selected from the formula (1) with, forexample, a monomer forming a (thio)urethane resin and/or an episulfideresin, and then polymerizing the monomers. The polymerization method ofthe raw material monomer is not particularly limited, and in general,cast polymerization is employed. Specifically, at least one kind of thebenzotriazole compound selected from the formula (1) may be mixed withthe raw material monomer, and then the mixed liquid may be charged in amold for forming a lens and heated to a temperature generally of from 20to 150° C., thereby providing the transparent plastic substrate.

As another production method of the transparent plastic substrate of thepresent invention, such a method may also be employed that at least onekind of the benzotriazole compound selected from the formula (1) and anappropriate surfactant are dissolved or dispersed in water, and atransparent plastic substrate is immersed therein to infiltrate thetransparent plastic substrate with the benzotriazole compound, therebyproviding the transparent plastic substrate.

The mixed liquid of the benzotriazole compound represented by theformula (1) and the raw material monomer for the transparent plasticsubstrate may contain depending on necessity a polymerization catalystdescribed in JP-A-07-063902, JP-A-07-104101, JP-A-09-208621,JP-A-09-255781 and the like, and an assistant, such as, an internalreleasing agent, an antioxidant, a fluorescent whitening agent and abluing agent, described in JP-A-01-163012, JP-A-03-281312 and the like.The transparent plastic substrate obtained in the present invention maybe subjected to a dyeing treatment using a colorant.

The transparent plastic member of the present invention contains thebenzotriazole compound represented by the formula (1), and may have, forexample, a functional layer, and preferably contains the transparentplastic substrate and a functional layer.

The transparent plastic member of the present invention is preferably aplastic lens, and more preferably a plastic lens for spectacles.

As the functional layer, at least one selected from a cured film, aprimer layer, an antireflection film and a water repellent film may beexemplified.

Specifically, for enhancing the scratch resistance, a cured film may beformed on the transparent plastic substrate by using a coating liquidcontaining an organosilicon compound and fine particles of an inorganicmaterial, such as, tin oxide, silicon oxide, zirconium oxide andtitanium oxide. For enhancing the impact resistance, a primer layercontaining a polyurethane as a main component may be provided. Forimparting an antireflection function, an antireflection film may beformed by using silicon oxide, titanium dioxide, zirconium oxide,tantalum oxide and the like. For enhancing the water repelling property,a water repellent film may be formed on the antireflection film by usingan organosilicon compound having a fluorine atom.

In the transparent plastic member of the present invention, the portionthereof that contains the benzotriazole compound represented by theformula (1) is not particularly limited, and the benzotriazole compoundmay be contained in any of the functional layer and the transparentplastic substrate. More specifically, the benzotriazole compound may becontained in any of the transparent plastic substrate, the cured film,the primer layer, the antireflection film, and the water repellent film.

The benzotriazole compound represented by the formula (1) is preferablycontained in the transparent plastic substrate.

As a method for producing the transparent plastic member having thebenzotriazole compound contained in the functional layer thereof, such amethod may be employed that at least one kind of the benzotriazolecompound selected from the formula (1), the resin components, anddepending on necessity a solvent and the like are mixed to prepare acomposition, and the composition is coated on at least one surface of aplastic lens substrate, and then cured to form the functional layer,thereby providing the transparent plastic member.

The transparent plastic member (or the transparent plastic substrate) ofthe present invention preferably has a cut rate of light in the blueregion of from 380 to 500 nm of 35% or more, and more preferably 40% ormore, and while not limited, preferably 60% or less, and more preferably50% or less.

The cut rate of light having a wavelength of 410 nm is preferably 50% ormore, and more preferably 60% or more.

The term transparent in the present invention means that a material istransparent to such an extent that the side therebehind can be viewed.

The transparent plastic substrate of the present invention preferablyhas a light transmittance in a wavelength range of from 400 to 700 nm of70% or more, more preferably 80% or more, and further preferably 90% ormore.

EXAMPLES

The present invention will be described specifically with reference toexamples, but the present invention is not limited to the examples. Aplastic lens will be described as an example of the transparent plasticmember. The plastic lenses thus obtained were measured for theproperties in the following manners.

(1) Measurement of Cut Rate of Light in Blue Region (Wavelength Range offrom 380 to 500 nm)

The transmittances in a wavelength range of from 380 to 500 nm weremeasured with a spectrophotometer (U-4100, produced by Hitachi, Ltd.),and the cut rate of blue light was calculated from the transmittances(T) of every 10 nm according to the following expression.

${{Blue}\mspace{14mu}{light}\mspace{14mu}{cut}\mspace{14mu}{rate}\mspace{14mu}(\%)} = {100 - \frac{\sum_{380\mspace{11mu} n\; m}^{500\mspace{11mu} n\; m}(T)}{13}}$(2) Measurement of Cut Rate at 410 nm

The light transmittance at a wavelength of 410 nm was measured with aspectrophotometer, and the cut rate of light was calculated according tothe following expression.Cut rate of light (%)=100−(transmittance at 410 nm)

Example 1

50.28 parts by mass of bis(isocyanatomethyl)bicyclo[2.2.1]heptane as araw material monomer for a lens, 0.06 part by mass of dimethyltindichloride as a catalyst, 0.15 part by mass of an acidic phosphateester, JP-506H (produced by Johoku Chemical Co., Ltd.), as a releasingagent, and 1.90 parts by mass of2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole asan ultraviolet ray absorbent were mixed by stirring, to which 25.50parts by mass of pentaerythritol tetrakis(3-mercaptopropionate) and24.22 parts by mass of 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane aslens raw materials were then further added, and the components weremixed by stirring under a reduced pressure of 10 mmHg for 30 minutes,thereby preparing a monomer composition for a lens. The monomercomposition for a lens was charged in a mold for molding a lens formedof a glass mold and a resin gasket (set to 0.00D and thickness of 1.6mm) provided in advance, and polymerized in an electric furnace at atemperature over 20° C. to 120° C. for 24 hours. After completing thepolymerization, the gasket and the mold were removed, and the resultingmolded article was heat-treated at 120° C. for 2 hours, therebyproviding a transparent plastic lens.

The results obtained by measuring the resulting lens for the cut rate at410 nm and the cut rate of blue light are shown in Table 1.

Examples 2 to 7 and Comparative Examples 1 and 2

Transparent plastic lenses were obtained in the same manner as inExample 1 except that the kinds and the amounts of the raw materialmonomer for a lens and the ultraviolet ray absorbent were changed asshown in Table 1.

The results obtained by measuring the resulting lenses for the cut rateat 410 nm and the cut rate of blue light are shown in Table 1.

Example 8

93.00 parts by mass of bis((3-epithiopropyl) sulfide and 1.00 part bymass of 2-hydroxyethyl methacrylate as raw materials for a lens, and0.40 part by mass of2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-211-benzotriazole asan ultraviolet ray absorbent were mixed by stirring, to which 6.00 partsby mass of n-butyl thioglycolate and 0.05 part by mass oftetra-n-butylphosphonium bromide as a catalyst were further added, andthe components were mixed by stirring under a reduced pressure of 10mmHg for 3 minutes, thereby preparing a monomer composition for a lens.The monomer composition for a lens was charged in a mold for molding alens formed of a glass mold and a resin gasket (set to 0.00D andthickness of 1.6 mm) provided in advance, and polymerized in an electricfurnace at a temperature over 20° C. to 100° C. for 20 hours. Aftercompleting the polymerization, the gasket and the mold were removed, andthe resulting molded article was heat-treated at 110° C. for 1 hour,thereby providing a transparent plastic lens.

The results obtained by measuring the resulting lens for the cut rate at410 nm and the cut rate of blue light are shown in Table 1.

Example 9

90.00 parts by mass of methyl methacrylate and 10.00 parts by mass ofethylene glycol dimethacrylate as raw materials for a lens, 1.00 part bymass of2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole asan ultraviolet ray absorbent, and 0.10 part by mass ofazobisisobutyronitrile as a thermal polymerization initiator were mixedby stirring, and the components were well agitated at room temperatureand then deaerated under a reduced pressure of 50 mmHg for 10 minutes.The monomer composition for a lens was charged in a mold for molding alens formed of a glass mold and a resin gasket (set to 0.00D andthickness of 1.6 mm) provided in advance, and polymerized in an electricfurnace at a temperature over 40° C. to 85° C. for 24 hours. Aftercompleting the polymerization, the gasket and the mold were removed, andthe resulting molded article was heat-treated at 100° C. for 2 hours,thereby providing a transparent plastic lens.

The results obtained by measuring the resulting lens for the cut rate at410 nm and the cut rate of blue light are shown in Table 1.

Example 10

To 100 parts by mass of polycarbonate resin powder, which was obtainedby polymerization by an ordinary interface polymerization of bisphenol Aand phosgene, 1.00 part by mass of2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole asan ultraviolet ray absorbent was added, sufficiently mixed with atumbler mixer, and then formed into pellets with a vent-type twin screwextruder having a diameter of 30 mm at a temperature of 290° C. and avacuum degree of 4.7 kPa. The resulting pellets were subjected toinjection compression molding, thereby providing a transparent plasticlens.

The results obtained by measuring the resulting lens for the cut rate at410 nm and the cut rate of blue light are shown in Table 1.

Comparative Example 3

A transparent plastic lens was obtained in the same manner as in Example8 except that 0.40 part by mass of2-(2-hydroxy-4-octyloxyphenyl)-2H-benzotriazole was used as anultraviolet ray absorbent.

The results obtained by measuring the resulting lens for the cut rate at410 nm and the cut rate of blue light are shown in Table 1.

TABLE 1 Cut Lens raw (proportion Cut rate material in 100 Ultravi- (partrate of monomer/ parts olet ray by at blue resin by mass) absorbentmass) 410 nm light Exam- M-1 50.28% U-1 1.90 99% 46% ple 1 M-2 25.50%M-3 24.22% Exam- M-1 50.28% U-1 1.00 99% 45% ple 2 M-2 25.50% M-3 24.22%Exam- M-4 52.02% U-1 0.20 87% 41% ple 3 M-3 47.98% Exam- M-5 47.54% U-21.20 99% 45% ple 4 M-6 26.46% M-7 26.00% Exam- M-5 47.54% U-3 2.00 87%40% ple 5 M-6 26.46% M-7 26.00% Exam- M-5 47.54% U-4 2.50 88% 41% ple 6M-6 26.46% M-7 26.00% Exam- M-4 52.02% U-1 0.10 69% 40% ple 7 M-3 47.98%Exam- M-8 93.00% U-1 0.40 99% 45% ple 8 M-9 1.00% M-10 6.00% Exam- M-1190.00% U-1 1.00 99% 45% ple 9 M-12 10.00% Exam- M-13 100.00% U-1 1.0099% 45% ple 10 Compar- M-1 50.28% U-5 1.00 35% 32% ative M-2 25.50%Exam- M-3 24.22% ple 1 Compar- M-4 52.02% U-5 0.50 35% 32% ative M-347.98% Exam- ple 2 Compar- M-8 93.00% U-5 0.40 32% 30% ative M-9 1.00%Exam- M-10 6.00% ple 3 Each monomer or resin, and each ultravioletabsorbent shown in the table are as follows. Monomer and Resin M-1:bis(isocyanatomethyl)bicyclo[2.2.1]heptane M-2: pentaerythritoltetrakis(3-mercaptopropionate) M-3:1,2-bis(2-mercaptoethylthio)-3-mercaptopropane M-4:bis(isocyanatomethyl)benzene M-5: bis(isocyanatomethyl)cyclohexane M-6:pentaerythritol tetrakismercaptoacetate M-7:2,5-bismercaptomethyl-1,4-dithiane M-8: bis(β-epithiopropyl) sulfideM-9: 2-hydroxyethyl methacrylate M-10: n-butyl thioglycolate M-11:methyl methacrylate M-12: ethylene glycol dimethacrylate M-13:polycarbonate resin Ultraviolet Absorbents U-1:2-(3-tert-butyl-2-hydroxy5-methylphenyl)-5-chloro-2H-benzotriazole U-2:2-(3-tert-butyl-2-hydroxy5-ethylphenyl)-5-chloro-2H-benzotriazole U-3:2-(4-ethoxy-2-hydroxyphenyl)-5-chloro-2H-benzotriazole U-4:2-(4-butoxy-2-hydroxyphenyl)-5-chloro-2H-benzotriazole U-5:2-(2-hydroxy-4-octyloxyphenyl)-2H-benzotriazole

While the plastic lenses are shown in the examples, the same effect canbe obtained by providing a transparent plastic member containing thebenzotriazole compound represented by the formula (1), for example, on adisplay screen of a personal computer, a mobile phone, a smartphone andthe like.

The invention claimed is:
 1. A method for producing transparent plasticsubstrate comprising: first mixing a polyisocyanate compound and abenzotriazole compound of formula (1-1),

wherein R₁ represents an alkyl group having from 1 to 3 carbon atoms oran alkoxy group having from 1 to 3 carbon atoms, m represents an integerof 0 or 1, and R₂ represents an alkyl group having from 1 to 12 carbonatoms or an alkoxy group having from 1 to 12 carbon atoms, provided thatin the case where m is 1, R₁ and R₂ may be the same as or different fromeach other, further mixing a polythiol compound with the mixtureobtained by the first mixing to obtain a monomer composition; andpolymerizing the monomer composition, wherein, in the first mixing, thebenzotriazole compound is mixed with the polyisocyanate compound in anamount of 0.10-2.00 parts by mass per 100 parts by mass of apredetermined total amount of the polyisocyanate compound and thepolythiol compound that is to be added in the second mixing.
 2. Themethod according to claim 1, further comprising: charging the monomercomposition in a mold for molding a lens before the polymerizing.
 3. Themethod according to claim 1, wherein the benzotriazole compound is atleast one selected from2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole,2-(3-tert-butyl-2-hydroxy-5-ethylphenyl)-5-chloro-2H-benzotriazole,2-(4-ethoxy-2-hydroxyphenyl)-5-chloro-2H-benzotriazole and2-(4-butoxy-2-hydroxyphenyl)-5-chloro-2H-benzotriazole.
 4. The methodaccording to claim 1, wherein the benzotriazole compound is at least oneselected from2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole and2-(3-tert-butyl-2-hydroxy-5-ethylphenyl)-5-chloro-2H-benzotriazole. 5.The method according to claim 1, wherein the transparent plasticsubstrate has a cut rate of light in a wavelength range of from 380 to500 nm of 35% or more.
 6. The method according to claim 1, wherein thetransparent plastic substrate has a cut rate of light having awavelength of 410 nm of 50% or more.
 7. The method according to claim 2wherein the benzotriazole compound is at least one selected from2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole,2-(3-tert-butyl-2-hydroxy-5-ethylphenyl)-5-chloro-2H-benzotriazole,2-(4-ethoxy-2-hydroxyphenyl)-5-chloro-2H-benzotriazole and2-(4-butoxy-2-hydroxyphenyl)-5-chloro-2H-benzotriazole.
 8. The methodaccording to claim 2, wherein the benzotriazole compound is at least oneselected from2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole and2-(3-tert-butyl-2-hydroxy-5-ethylphenyl)-5-chloro-2H-benzotriazole. 9.The method according to claim 2, wherein the transparent plasticsubstrate has a cut rate of light in a wavelength range of from 380 to500 nm of 35% or more.
 10. The method according to claim 2, wherein thetransparent plastic substrate has a cut rate of light having awavelength of 410 nm of 50% or more.
 11. A method for producingtransparent plastic substrate comprising: first mixing a polyisocyanatecompound, at least one of a catalyst and a releasing agent, and abenzotriazole compound of formula (1-1),

wherein R₁ represents an alkyl group having from 1 to 3 carbon atoms oran alkoxy group having from 1 to 3 carbon atoms, m represents an integerof 0 or 1, and R₂ represents an alkyl group having from 1 to 12 carbonatoms or an alkoxy group having from 1 to 12 carbon atoms, provided thatin the case where m is 1, R₁ and R₂ may be the same as or different fromeach other; further mixing a polythiol compound with the mixtureobtained by the first mixing to obtain a monomer composition; andpolymerizing the monomer composition, wherein, in the first mixing, thebenzotriazole compound is mixed with the polyisocyanate compound in anamount of 0.10-2.00 parts by mass per 100 parts by mass of apredetermined total amount of the polyisocyanate compound and thepolythiol compound that is to be added in the second mixing.
 12. Themethod according to claim 11, wherein the polyisocyanate compound, thecatalyst, the releasing agent, and the amount of benzotriazole compoundare mixed in the first mixing at the same time.
 13. The method accordingto claim 11, wherein the polyisocyanate compound comprisespolyisocyanate having an aromatic ring, and the polythiol compoundcomprises aliphatic thiol.